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Proanthocyanidin

Family: Plantae - Tamaricaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavanol Dimer

Canonical Smiles	COc1c(O)cc(cc1O)C1Oc2c(C[C@H]1O)c(O)cc(c2[C@@H]1[C@@H](O)[C@H](Oc2c1c(O)cc(c2)O)c1ccc(cc1)O)O
InChI	InChI=1S/C31H28O12/c1-41-31-20(37)6-13(7-21(31)38)28-22(39)10-16-17(34)11-19(36)25(30(16)43-28)26-24-18(35)8-15(33)9-23(24)42-29(27(26)40)12-2-4-14(32)5-3-12/h2-9,11,22,26-29,32-40H,10H2,1H3/t22-,26-,27-,28?,29-/m1/s1
InChIKey	JPFCOVZKLAXXOE-XBNSMERZSA-N
Formula	C₃₁H₂₈O₁₂
HBA	12
HBD	9
MW	592.55
Rotatable Bonds	4
TPSA	209.76
LogP	3.3
Number Rings	6
Number Aromatic Rings	4
Heavy Atom Count	43
Formal Charge	0
Fraction CSP3	0.23
Exact Mass	592.16
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Tamarix articulata	Tamaricaceae	Plantae	189786

Showing of synonyms

Shaalan Y.M, Handoussa H, et al. (2018). Destabilizing the interplay between miR-1275 and IGF2BPs by Tamarix articulata and quercetin in hepatocellular carcinoma. Nat Prod Res,2018,32(18),2217-2220. [View] [PubMed]

Pubchem: 108065

Nmrshiftdb2: 60026397

Comptox: DTXSID00276046

CPRiL: 36619

SMILES: c1ccccc1C(O2)CCc(c23)cccc3C4CC(c5ccccc5)Oc(c46)cccc6

Level: 3

Mol. Weight: 592.55 g/mol

SMILES: c1ccccc1C(O2)CCc(c23)cccc3C4CCOc(c45)cccc5

Level: 2

Mol. Weight: 592.55 g/mol

SMILES: O1CCCc(c12)cccc2C3CC(c4ccccc4)Oc(c35)cccc5

Level: 2

Mol. Weight: 592.55 g/mol

SMILES: O1CCCc(c12)cccc2C3CCOc(c34)cccc4

Level: 1

Mol. Weight: 592.55 g/mol

SMILES: c1cccc(c12)OC(CC2)c3ccccc3

Level: 1

Mol. Weight: 592.55 g/mol

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 592.55 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 592.55 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.41
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.500
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 12.94

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.840
Plasma Protein Binding: 74.93
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 11.090
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.490
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.150
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.300
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -19522.930
Rat (Acute): 2.360
Rat (Chronic Oral): 4.270
Fathead Minnow: 41.910
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 468.140
Hydration Free Energy: -3.170
Log(D) at pH=7.4: 2.330
Log(P): 1.81
Log S: -5.61
Log(Vapor Pressure): -15.93
Melting Point: 255.22
pKa Acid: 7.71
pKa Basic: 5.09

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.9111
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.9067
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8934
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8831
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8601
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8592
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8408
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.8407
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8361
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8337
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8315
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	4	0.8268
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8177
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.8156
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.8154
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.8113
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8055
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7641
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7629
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7627
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7623
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7553
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7548
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7531
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7494
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7438
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	4	0.7399
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7358
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.7279
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7214
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7213
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7201
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7182
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7160
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7152
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7136
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7060
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7053
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7050
Reticuline oxidase	P30986	RETO_ESCCA	Eschscholzia californica	5	0.7047
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7044
Carnitine O-palmitoyltransferase 2, mitochondrial	P18886	CPT2_RAT	Rattus norvegicus	3	0.7039
dTDP-4-dehydrorhamnose 3,5-epimerase	A0A6L7H6N0	A0A1S0QLH9_BACAN	Bacillus anthracis	3	0.7034
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7027
Geranylgeranyl transferase type-2 subunit alpha	Q08602	PGTA_RAT	Rattus norvegicus	4	0.7026
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	4	0.7014

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